Sodium Hydroxide → 2(1H)-Pyridinone, 3-((4-(2-(3-(methylsulfonyl)-2-thienyl)ethyl)-1-piperidinyl)methyl)-

HRID 1837745ノート

反応式

HRID 1837745 の反応式
C[O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17][C:18]3[S:19][CH:20]=[CH:21][C:22]=3[S:23]([CH3:26])(=[O:25])=[O:24])[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][N:4]=1.S(Cl)(Cl)=O.[OH-].[Na+]>C(O)C>[O:2]=[C:3]1[C:8]([CH2:9][N:10]2[CH2:11][CH2:12][CH:13]([CH2:16][CH2:17][C:18]3[S:19][CH:20]=[CH:21][C:22]=3[S:23]([CH3:26])(=[O:25])=[O:24])[CH2:14][CH2:15]2)=[CH:7][CH:6]=[CH:5][NH:4]1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 22678292HCID 22678292、化合物

生成物 1

HCID 226782962(1H)-Pyridinone, 3-((4-(2-(3-(methylsulfonyl)-2-thienyl)ethyl)-1-piperidinyl)methyl)-収率 83.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

6.09 g of 1-[(2-methoxy-3-pyridyl)methyl]-4-[2-(3-methylsulfonyl-2-thienyl)ethyl]piperidine obtained in Example 43 and 2 ml of thionyl chloride were dissolved in 50 ml of ethanol, and the mixture was heated under reflux for 2 hours. The reaction mixture was basified by adding a 1N aqueous sodium hydroxide thereto, and then extracted with dichloromethane. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting crude product was purified by NH form silica gel column chromatography (ethyl acetate), to give 4.89 g of the title compound as colorless crystals.

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe resulting crude product was purified by NH
  8. customform silica gel column chromatography (ethyl acetate)

出典と根拠

ORDレコード
ord-00ca5ea8d27945e7b67f204378a39566
出典データセット
uspto-grants-2004_08
特許番号
US06784192B2

反応ノート

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